Santa's Favorite Helper
by anufoalan
Summary: What happens when Oliver needs a date, and someone decides to help him out.


I own nothing

Present

How did they get here, he thought. He had her pinned beneath him finally after months maybe years of wanting her, and it had all started with a sprained ankle.

Two weeks earlier

"Please Chloe?"

"No"

"Please."

"No."

"I wouldn't ask if it wasn't necessary."

"No, I don't care it's not going to happen, I repeat NO!"

"Come on Chloe, she sprained he ankle and I'm dateless for the event, think about all those poor children, please."

"Oliver, I'm sure you have a little black book full of names who you can take to this thing."

"None of them would even speak to me.

"Come on Chloe please? I'll buy you a year's supply of coffee." Oliver offered hopefully.

He could tell that her resolve was weakening.

"A year's supply of coffee and a brand new laptop only the best."

"Fine Queen but I expect them on my desk first thing the next morning."

Two Hours Earlier

She pulled down the hemline of the dress one last time before she made her way to the door. Taking a deep breath before she opened it and stepped out into the Watchtower, she mentally prepared herself. Tonight was the big children's benefit for the Metropolis Children's Hospital. Not a typical black tie event that she would have expected Oliver to attend, no it was a costume ball. Not just any costume ball either... a themed costume ball, everyone had to be decked out in a holiday themed costume. And now here she was getting ready to join her date in the most ridiculous outfit ever.

She rolled her eyes she never should have let Lois take her shopping for this ridiculous scrap of material. She was decked out as "Santa's favourite little helper" Santa's little home wrecker is more like it she had told Lois when she saw the red and white candy stripped dress and red fish net combination. But then again this was Lois the same woman who had been dropping hints repeatedly during their shopping trip for Chloe to just jump Ollie and go at it like a pair of rabid bunnies, not that Chloe didn't want to, but Ollie would never see her that way she sighed, just like every other man. He wouldn't even be taking her to the event if his date hadn't gotten injured and his little black book hadn't gone up in flames, after all she was his last choice.

Oliver was wondering what was taking her so long, it wasn't like she had to put on a ball gown or anything, he sighed to himself. If he were invited to any normal costume benefit he would be dressed as Robin Hood but due to the theme of the party, he was dressed as a younger version of Santa as he just didn't think he could pull of a beard and belly.

"Chloe could you please hurry up or we're going to be late!" Oliver yelled

Chloe walked out of the bedroom and Oliver's jaw hit the floor.

"Wow Sidekick if I had of known you cleaned up that good I would have come to you first for a date!"

"Oliver I look like a skanky candy cane threw up on me."

"What! No Chloe you look great"

Chloe just glared at Oliver.

"Let's get this over with quickly so that I can get out of this ridiculous outfit."

As Oliver led Chloe into the ballroom Chloe was amazed and relived, luckily for her she wasn't the only person there dressed in a similar fashion. The ballroom was decked out in holiday cheer and there were a variety of entertainment around the room, from acrobats to a hypnotist.

"Wow, Ollie this is incredible."

"I know. When I accepted the invitation I never expected this. I think that the kids are going to do very well this year."

Chloe and Oliver circulated the room making their donation to the charity and finally coming to a stop in front of the hypnotist. Suddenly the hypnotist called Chloe forward and after much resisting she went. After a few average suggestions and having them been lifted he was about to send her back when he noticed the way Oliver was looking at her and decided that after all Christmas was the season of giving.

Before sending Chloe back Oliver noticed that the hypnotist whispered something in her ear.

"So, what did he say?"

"Huh, oh nothing Oliver it was nothing."

The evening continued uneventfully and they went home to the Clocktower where Chloe was staying the night.

"Come on Watchtower let's get you to bed."

The next thing Oliver knew Chloe was kissing him. He had been dreaming of this for a while but he was wondering where it came from.

Little did Oliver know the last thing that the hypnotist had said to Chloe was that when the word bed was mentioned that she would reveal her feelings for her date.

Oliver picked her up and stumbled through the apartment unfortunately he couldn`t make it all the way to the bedroom and stumbled back into a chair pulling Chloe down into his lap he continued to kiss her.

"What brought this on Sidekick?"

"I want you Ollie."

Surprised Oliver didn't know what to say, instead he picked Chloe up and finally made it the rest of the way to the bedroom. Once there he stripped her dress off followed by his shirt. Once it was off Oliver finally noticed what Chloe was wearing underneath. A red and green stripper bra and panty set to go with the stockings and the red heels that she had worn that night.

"Chloe," was all that Oliver managed to get out as she had managed to scramble his brain.

Standing with one hand on her hip she beckoned to him with her finger.

"Do you see something you like Arrow?"

All he could do was nod walking towards her and backing her towards the bed he managed to remove her bra before she fell back on the bed. He then proceeded to remove her shoes, stockings and panties before kissing down her body to the apex of her thighs where he ever so gently stroked her womanhood with his tongue and sucked her clit into his mouth. Chloe gripped his hair and thrashed on the bed as he pleasures her body almost coming off the bed when he inserted a finger into her womanhood and started thrusting. All she could do was moan as he pleasured her. Inserting a second finger and crooking then he rub against the dense spot of tissue deep inside of her. She cried out as she came tightening on his fingers as he continued to lap at her.

When she finally stopped quivering he slid up her body and kissed her.

"So how was that Sidekick?"

"Amazing, but I think you can still do better."

Smirking he got up and removed his pants and lay back down on the bed next to her caressing her body he continued to kiss her and eventually returned his fingers to her womanhood groaning when he felt how wet she was.

"Ollie, please I want you in me now"

With that one statement he rolled over her and thrust into her groaning at how tight she was. After giving her a moment to adjust to his size he started thrusting slowly. Moaning as she thrust in time with him. Feeling a sparking in his spine he reached one hand down and rubbing her clit as he continued to thrust, Chloe started tightening around him and he knew that she was as close as he is with half a dozen more thrusts she came screaming his name, and a few thrusts later he spilled his seed inside her as she milked him for all that he had.

As he slid out of her with a sigh and rolled over to lie next to her, he wrapped his arm around her waist and held her against him.

"Chloe, this better not be a onetime thing because I don't think I can do that."

But as he turned to hear her answer he discovered she was asleep, her answer would have to wait till morning.

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